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Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Greenwood holiday rentals

An outdoor patio with stone flooring, string lights, and various plants.

1. Guesthouse

Guesthouse
Crozet
10.0 out of 10, Exceptional, (93 reviews)
"Really cute place, nicely appointed and comfortable."
United States
Laurie R.
The price is AU$347
includes taxes & fees
15 Nov - 16 Nov
Guesthouse
A blue door with a keyhole and a sign for 'Stay in Crozet' overnight lodging.

2. Stay in Crozet Mountain Suite in Downtown Crozet

Stay in Crozet Mountain Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (131 reviews)
"We enjoyed our stay and our host Amy was very accommodating and easy to reach."
United States
Lynn K.
The price is AU$375
includes taxes & fees
12 Nov - 13 Nov
Stay in Crozet Mountain Suite in Downtown Crozet
Street view

3. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (282 reviews)
"Clean room convenient parking, good kitchen, friendly staff."
United States
Jamie
The price is AU$183
includes taxes & fees
24 Nov - 25 Nov
Valley Extended Suites
A blue door with a keyhole and a sign for 'Stay in Crozet' overnight lodging.

4. Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (74 reviews)
"Great communication and clear details. Awesome spot for the Crozet area. Easy walking to dining options."
United States
Brian
The price is AU$377
includes taxes & fees
29 Nov - 30 Nov
Stay in Crozet Train Suite in Downtown Crozet
A cafe interior with a wooden floor, a bar area, and a seating section with a large mirror and a brown leather chair.

5. High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (116 reviews)
"perfect location to montfair resort where we attended wedding...coffee within walking distance, very clean house, kitchen well stocked, had a fantastic time ..highly recommend you visit here for your stay..."
United States
karen r.
The price is AU$510
includes taxes & fees
16 Nov - 17 Nov
High Street | Walk to Everything Crozet | Pet-Friendly
A wooden deck with a table and chairs, surrounded by lush greenery.

6. Wandering Bear’s Den Private Studio Near Crozet and Charlottesville

Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
Charlottesville
9.8 out of 10, Exceptional, (70 reviews)
"What a wonderful retreat! It had everything we needed, was clean and comfortable and afforded us tranquility after working our booth at a local art fair. We look forward to staying there again. We did have a challenge trying to unlock the door upon arrival, but a quick call to the owner took care of that."
United States
Fay
The price is AU$228
includes taxes & fees
17 Nov - 18 Nov
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
An outdoor seating area with wooden chairs and a central fire pit, surrounded by a stone wall and a building with a red roof.

7. The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (42 reviews)
"A lovely place to stay and relax! Not far to get to wineries and to Charlottesville. Thank you for a lovely stay!"
United States
Mary R.
The price is AU$434
includes taxes & fees
16 Nov - 17 Nov
The Cottage @ Afton Mountain- Close to Wineries!
A log cabin with a red door, a welcome sign, and a window with a hanging flower arrangement.

8. Willow Haven: Cozy cabin in delightful Afton

Willow Haven: Cozy cabin in delightful Afton
Afton
9.8 out of 10, Exceptional, (49 reviews)
"Great little cabin"
United States
Travis W.
The price is AU$330
includes taxes & fees
21 Nov - 22 Nov
Willow Haven: Cozy cabin in delightful Afton
A covered patio with a round table and chairs, a sofa, and a view of a grassy yard through large windows.

9. Rosé All Day: Wine Country Getaway! Walk to Dining

Rosé All Day: Wine Country Getaway! Walk to Dining
Crozet
9.8 out of 10, Exceptional, (35 reviews)
"Fantastic stay. Happy to return next time."
United States
Sam B.
The price is AU$611
includes taxes & fees
15 Nov - 16 Nov
Rosé All Day: Wine Country Getaway! Walk to Dining
A cozy cabin interior with wooden walls, a TV on a wooden stand, a sofa, and a staircase.

10. Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC

Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC
Afton
10.0 out of 10, Exceptional, (21 reviews)
"Cute property that was super clean and comfortable! Enjoyed our stay and would definitely visit again!"
United States
Kevin
The price is AU$389
includes taxes & fees
17 Nov - 18 Nov
Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC
A rustic wooden building with a steeply pitched roof, a central entrance with a door, and a small window above the door.

11. Ivy Rose Cottage nestled b/t Cville & Vineyards

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (98 reviews)
"The home was comfortable, quaint, and unique. Everything was in order upon arrival and the stay was overall enjoyable."
United States
Joel F.
The price is AU$462
includes taxes & fees
16 Nov - 17 Nov
Ivy Rose Cottage nestled b/t Cville & Vineyards
A hot tub on a wooden deck with a wooden railing and a table with chairs.

12. Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
9.6 out of 10, Exceptional, (17 reviews)
"Our stay was fantastic! Great location for wineries and hiking. Perfect for a couples getaway for privacy and quaintness. Will definitely consider booking again if we ever come back to the area!! "
United States
Liz D.
The price is AU$475
includes taxes & fees
3 Dec - 4 Dec
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

13. Unique Cypress cottage, close to Charlottesville with mountain views.

Unique Cypress cottage, close to Charlottesville with mountain views.
Charlottesville
10.0 out of 10, Exceptional, (69 reviews)
"Beautiful place and easy access to wineries and breweries in the area! The cottage was very clean, cozy and accommodating. Will come again!"
United States
Allison H.
The price is AU$390
includes taxes & fees
17 Nov - 18 Nov
Unique Cypress cottage, close to Charlottesville with mountain views.
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

14. Petite Pink Cottage, Perfect for Solo Travelers

Petite Pink Cottage, Perfect for Solo Travelers
Charlottesville
10.0 out of 10, Exceptional, (10 reviews)
"A very special, unique property. We enjoyed our stay in the cozy, cute, clean cottage. Great location. We will return again."
United States
Tracy
The price is AU$664
includes taxes & fees
12 Nov - 13 Nov
Petite Pink Cottage, Perfect for Solo Travelers
A two-story house with a porch, a front door, and a mailbox.

15. Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom

Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
Charlottesville
9.4 out of 10, Exceptional, (16 reviews)
"Looks brand new and very clean. Nice place."
United States
Ron C.
The price is AU$284
includes taxes & fees
17 Nov - 18 Nov
Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
A hallway with a wooden floor, a patterned rug, a wooden bench, a chair, a wooden cabinet, and a door with windows.

16. Mountain View Cottage | Wine, Hiking & Dog Friendly

Mountain View Cottage | Wine, Hiking & Dog Friendly
Afton
9.8 out of 10, Exceptional, (57 reviews)
"A beautiful inviting place to stay! Great communication from check in to check out."
United States
Dustin S.
The price is AU$1,543
includes taxes & fees
14 Nov - 15 Nov
Mountain View Cottage | Wine, Hiking & Dog Friendly
A spacious kitchen with a large island, dark cabinetry, and a stone pendant light.

17. Mountain Mama- Amazing Views! + Hot Tub!

Mountain Mama- Amazing Views! + Hot Tub!
Afton
9.8 out of 10, Exceptional, (30 reviews)
"Terrific home. Incredibly spacious and well laid out for comfort and privacy!"
United States
Maura F.
The price is AU$777
includes taxes & fees
15 Nov - 16 Nov
Mountain Mama- Amazing Views! + Hot Tub!
A compact kitchen with white cabinetry, a blue door, and a white refrigerator.

18. Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (59 reviews)
"It was a couple very cozy place for us to stay in the perfect location."
United States
Linda W.
The price is AU$320
includes taxes & fees
1 Dec - 2 Dec
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
A house with a white exterior, a window with a hanging plant, and a garden with hydrangea flowers.

19. The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Waynesboro
10.0 out of 10, Exceptional, (26 reviews)
"Great host and beautifully decorated property."
United States
Elisa G.
The price is AU$260
includes taxes & fees
16 Nov - 17 Nov
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

20. Charming Cottage Near Vineyards

Charming Cottage Near Vineyards
Charlottesville
10.0 out of 10, Exceptional, (12 reviews)
"Loved this place for a short getaway. Great location!"
United States
Nicole M.
The price is AU$874
includes taxes & fees
24 Nov - 25 Nov
Charming Cottage Near Vineyards
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Find holiday rentals that suit your style

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Find out more about Greenwood

Everything you need to know about Greenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Greenwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood holiday rentals we have selected for you start as low as AU$181 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its wineries.

What are some of the best holiday rentals that Greenwood has to offer?

RiverFront Country Home with Blue Mountain Views: This holiday home rental outside of Greenwood is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Greenwood?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Greenwood stay.

What’s there to see and do in Greenwood?

Explore the area and family-friendly sights such as Virginia Discovery Museum, or get out into nature at a spot like Rockfish Gap Entrance Shenandoah. In the wider area, you’ll find Pollak Vineyards and King Family Vineyards.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.